The present invention relates to uracil compounds and use thereof.
An object of the present invention is to provide compounds having excellent herbicidal activity.
Currently, a lot of herbicides are commercially available and used, however since there are many kinds of weeds to be controlled and generation thereof ranges over a long period, there is requirement a herbicide which have higher herbicidal effect, have a wide range of herbicidal spectrum, and causes no phytotoxicity on crops.
U.S. Pat. No. 4,859,229, WO92/11244, WO97/01541, WO97/05116, WO98/41093 and the like disclose that certain kinds of phenyluracil compounds have herbicidal activity, however, these phenyluracil compounds do not have sufficient abilities as a herbicide.
The present inventors have intensively studied to find a compound having excellent herbicidal activity, and resultantly, found that uracil compounds of the following formula [I] have excellent herbicidal activity, leading to completion of the present invention. Namely, the present invention provides uracil compounds of the formula [I] (hereinafter, referred to as the present compound): 
[wherein, Q-R3 represents a R3-substituted group of a 5-membered or 6-membered heterocyclic ring having one or two nitrogen selected from the group consisting of moieties represented by the following formulae 
(wherein, this heterocyclic ring may be substituted with at least one kind of substituent selected from the group consisting of halogen, C1 to C6 alkyl, C1 to C6 haloalkyl, C2 to C6 alkenyl, C2 to C6 haloalkenyl, C2 to C6 alkynyl, C2 to C6 haloalkynyl, C1 to C6 alkoxy C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 haloalkoxy, C1 to C6 alkoxycarbonyl C1 to C6 alkoxy, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, cyano, hydroxy, mercapto, oxo and thioxo.), Y represents oxygen, sulfur, imino or C1 to C3 alkylimino, R1 represents C1 to C3 alkyl or C1 to C3 haloalkyl, R2 represents C1 to C3 alkyl, R3 represents carboxy C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl, C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkynyloxycarbonyl C1 to C6 alkyl, OR7, SR8 or N(R9)R10, X1 represents halogen, cyano, thiocarbamoyl or nitro, X2represents hydrogen or halogen.
{wherein, each of R7, R8 and R10 independently represents carboxy C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl, C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl, C3 to C6 haloalkynyloxycarbonyl C1 to C6 alkyl, C3 to C8 cycloalkoxycarbonyl C1 to C6 alkyl, C3 to C8 halocycloalkoxycarbonyl C1 to C6 alkyl, C3 to C8 cycloalkenyloxycarbonyl C1 to C6 alkyl, C3 to C8 halocycloalkenyloxycarbonyl C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C8 alkylidenaminoxycarbonyl C1 to C6 alkyl, phenoxycarbonyl C1 to C6 alkyl which may be substituted, phenyl C1 to C4 alkoxycarbonyl C1 to C6 alkyl which may be substituted, C1 to C6 alkoxyaminocarbonyl C1 to C6 alkyl, (C1 to C6 alkoxy)(C1 to C3 alkyl)aminocarbonyl C1 to C6 alkyl, C1 to C6 alkylaminocarbonyl C1 to C6 alkyl, (C1 to C6 alkyl) C1 to C6 alkylaminocarbonyl C1 to C6 alkyl, phenylaminocarbonyl C1 to C6 alkyl which may be substituted, or phenyl C1 to C4 alkylaminocarbonyl C1 to C6 alkyl which may be substituted, and R9 represents hydrogen or C1 to C6 alkyl.}.], and herbicides containing each of them as an effective ingredient.
In the present invention, as the group represented by Q-R3, for example, there are listed groups of the following formulae: 
[wherein, R3 is the same as defined above, each of Z1 and Z2 independently represents hydrogen, halogen, C1 to C6 alkyl, C1 to C6 haloalkyl, C2 to C6 alkenyl, C2 to C6 haloalkenyl, C2 to C6 alkynyl, C2 to C6 haloalkynyl, C1 to C6 alkoxy C1 to C6 alkyl, C1 to C6 alkoxy, C1 to C6 haloalkoxy, C1 to C6 alkoxycarbonyl C1 to C6 alkoxy or cyano (wherein, the halogen represented by Z1 or Z2 means fluorine, chlorine, bromine or iodine, and examples of the C1 to C6 alkyl include methyl, ethyl, propyl, isopropyl, butyl, s-butyl, t-butyl and the like, examples of the C1 to C6 haloalkyl include bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, trichloromethyl, difluoromethyl, chlorodifluoromethyl, bromodifluoromethyl, trifluoromethyl, pentafluoroethyl, 2-fluoroethyl, 1,1-difluoroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl and the like, examples of the C2 to C6 alkenyl include allyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-butenyl, 2-butenyl, 3-butenyl and the like, examples of the C2 to C6 haloalkenyl include 1-chloroallyl, 1-bromoallyl, 2-chloroallyl, 3,3-dichloroallyl and the like, examples of the C2 to C6 alkynyl include 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-butynyl and the like, examples of the C2 to C6 haloalkynyl include 3-bromo-2-propynyl, 3-iodo-2-propynyl, 1-fluoro-2-propynyl, 1-chloro-2-propynyl, 1-bromo-2-propynyl, 1-chloro-2-butynyl and the like, examples of the C1 to C6 alkoxy C1 to C6 alkyl include methoxymethyl, 2-methoxyethyl, 1-methoxyethyl, 3-methoxypropyl, ethoxymethyl, 2-ethoxyethyl, 3-ethoxypropyl, isopropoxymethyl, 2-isopropoxyethyl and the like, examples of the C1 to C6 alkoxy include methoxy, ethoxy, propoxy, isopropoxy, butyloxy, s-butyloxy, t-butyloxy and the like, examples of the C1 to C6 haloalkoxy include chloromethoxy, bromomethoxy, dichloromethyloxy, trichloromethyloxy, trifluoromethyloxy, 2-fluoroethyloxy, 2,2,2-trichloroethyloxy and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkoxy include methoxycarbonylmethoxy, ethoxycarbonylmethoxy, propoxycarbonylmethoxy, isopropoxycarbonylmethoxy, 1-methoxycarbonylethoxy, 1-ethoxycarbonylethoxy, 1-propoxycarbonylethoxy, 1-isopropoxycarbonylethoxy, 2-methoxycarbonylethoxy, 2-ethoxycarbonylethoxy, 2-propoxycarbonylethoxy, 2-isopropoxycarbonylethoxy and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-t-butoxycarbonylethyl and the like.).].
Examples of the carboxy C1 to C6 alkyl represented by R3 include carboxymethyl, 1-carboxyethyl, 2-carboxyethyl and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-t-butoxycarbonylethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl and the like, examples of the C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl include chloromethyloxycarbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloropropyloxycarbonylmethyl, 1-chloro-2-propyloxycarbonylmethyl, 2,2,2-trifluoroethyloxycarbonylmethyl and the like, examples of the C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl include allyloxycarbonylmethyl, 1-methyl-2-propenyloxycarbonylmethyl, 2-methyl-2-propenyloxycarbonylmethyl, 2-butenyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 1-(1-methyl-2-propenyloxycarbonyl)ethyl, 1-(2-methyl-2-propenyloxycarbonyl)ethyl, 2-allyloxycarbonylethyl, 2-(2-methyl-2-propenyloxycarbonyl)ethyl and the like, examples of the C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl include 1-chloroallyloxycarbonylmethyl, 1-(1-chloroallyloxycarbonyl)ethyl, 2-chloroallyloxycarbonylmethyl, 1-(2-chloroallyloxycarbonyl)ethyl and the like, examples of the C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl include propargyloxycarbonylmethyl, 1-methyl-2-propynyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 1-(1-methyl-2-propynyloxycarbonyl)ethyl, 2-propargyloxycarbonylethyl, 2-(1-methyl-2-propynyloxycarbonyl)ethyl and the like, examples of the C3 to C6 haloalkynyloxycarbonyl C1 to C6 alkyl include (3-chloro-2-propynyloxycarbonyl)methyl, 1-(3-chloro-2-propynyloxycarbonyl)ethyl, (1-chloro-2-propynyloxycarbonyl)methyl, 1-(1-chloro-2-propynyloxycarbonyl)ethyl and the like,
examples of the C1 to C3 alkylimino represented by Y include methylimino, ethylimino and the like,
the C1 to C3 alkyl represented by R2 means methyl, ethyl, propyl, isopropyl, and examples of the C1 to C3 haloalkyl include bromomethyl, chloromethyl, fluoromethyl, dichloromethyl, chlorodifluoromethyl, trichloromethyl, difluoromethyl, trifluoromethyl, pentafluoroethyl, 1,1-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl and the like,
the C1 to C3 alkyl represented by R2 means methyl, ethyl, propyl or isopropyl,
examples of the carboxy C1 to C6 alkyl represented by R7, R8 or R10 include carboxymethyl, 1-carboxyethyl, 2-carboxyethyl and the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkyl include methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, isobutoxycarbonylmethyl, s-butoxycarbonylmethyl, t-butoxycarbonylmethyl, amyloxycarbonylmethyl isoamyloxycarbonylmethyl, t-amyloxycarbonylmethyl, 1-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 1-propoxycarbonylethyl, 1-isopropoxycarbonylethyl, 1-butoxycarbonylethyl, 1-isobutoxycarbonylethyl, 1-s-butoxycarbonylethyl, 1-t-butoxycarbonylethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, and the like, examples of the C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl include chloromethyloxycarbonylmethyl, 2-fluoroethyloxycarbonylmethyl, 2-chloropropyloxycarbonylmethyl, 1-chloro-2-propyloxycarbonylmethyl, 2,2,2-trifluoroethyloxycarbonylmethyl and the like, examples of the C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl include allyloxycarbonylmethyl, 1-methyl-2-propenyloxycarbonylmethyl, 2-methyl-2-propenyloxycarbonylmethyl, 2-butenyloxycarbonylmethyl, 1-allyloxycarbonylethyl, 1-(1-methyl-2-propenyloxycarbonyl)ethyl, 1-(2-methyl-2-propenyloxycarbonyl)ethyl, 2-allyloxycarbonylethyl, 2-(1-methyl-2-propenyloxycarbonyl)ethyl, 2-(2-methyl-2-propenyloxycarbonyl)ethyl and the like, examples of the C3 to C6 haloalkenyloxycarbonyl C1 to C6 alkyl include 1-chloro-2-propenyloxycarbonylmethyl, 1-(2-chloro-2-propenyloxycarbonyl)ethyl and the like, examples of the C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl include propargyloxycarbonylmethyl, 1-methyl-2-propynyloxycarbonylmethyl, 1-propargyloxycarbonylethyl, 1-(1-methyl-2-propynyloxycarbonyl)ethyl, 2-propargyloxycarbonylethyl, 2-(1-methyl-2-propynyloxycarbonyl)ethyl and the like, examples of the C3 to C6 haloalkynyloxycarbonyl C1 to C6 alkyl include 1-bromo-2-propynyloxycarbonyl methyl, 1-(1-chloro-2-propynyloxycarbonyl)ethyl and the like, examples of the C3 to C8 cycloalkoxycarbonyl C1 to C6 alkyl include cyclopropyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, 1-(cyclobutyloxycarbonyl)ethyl and the like, examples of the C3 to C8 halocycloalkoxycarbonyl C1 to C6 alkyl include 2,2-difluorocyclopentyloxycarbonylmethyl, 2-bromocyclopentyloxycarbonylmethyl, 1-(2-chlorocyclobutyloxycarbonyl)ethyl and the like, examples of the C3 to C8 cycloalkenyloxycarbonyl C1 to C6 alkyl include 2-cyclopentenyloxycarbonylmethyl, 1-(2-cyclobutenyloxycarbonyl)ethyl and the like, examples of the C3 to C8 halocycloalkenyloxycarbonyl C1 to C6 alkyl include 4-bromo-2-cyclobutenyloxycarbonylmethyl and 1-(4-bromo-2-cyclopentenyloxycarbonyl)ethyl the like, examples of the C1 to C6 alkoxycarbonyl C1 to C6 alkoxycarbonyl C1 to C6 alkyl include methoxycarbonylmethoxycarbonylmethyl, 2-(methoxycarbonyl)-2-propoxycarbonylmethyl, 1-[1-(ethoxycarbonyl)ethoxycarbonyl]ethyl and the like, examples of the C1 to C8 alkylidenaminoxycarbonyl C1 to C6 alkyl include isoprpylidenaminoxycarbonylmethyl, 2-(isoprpylidenaminoxycarbonyl)ethyl and the like, examples of the phenoxycarbonyl C1 to C6 alkyl which may be substituted include phenoxycarbonylmethyl, 1-phenoxycarbonylethyl and the like, examples of the phenyl C1 to C4 alkoxycarbonyl C1 to C6 alkyl which may be substituted include benzyloxycarbonylmethyl, 1-benzyloxycarbonylethyl and the like, examples of the C1 to C6 alkoxyaminocarbonyl C1 to C6 alkyl include methoxyaminocarbonylmethyl, 1-methoxyaminocarbonylethyl, ethoxyaminocarbonylmethyl, 1-ethoxyaminocarbonylethyl and the like, examples of the (C1 to C6 alkoxy)(C1 to C3 alkyl)aminocarbonyl C1 to C6 alkyl include (methoxy)(methyl)aminocarbonylmethyl, 1-(methoxy)(methyl)aminocarbonylethyl, (ethoxy)(methyl)aminocarbonylmethyl, 1-(ethoxy)(methyl)aminocarbonylethyl and the like, examples of the C1 to C6 alkylaminocarbonyl C1 to C6 alkyl include methylaminocarbonylmethyl, ethylaminocarbonylmethyl, isopropylaminocarbonylmethyl, 1-methylaminocarbonylethyl, 1-isobutylaminocarbonylethyl and the like, examples of the (C1 to C6 alkyl)(C1 to C6 alkyl)aminocarbonyl C1 to C6 alkyl include dimethylaminocarbonylmethyl, 1-dimethylaminocarbonylethyl and the like, examples of the phenylaminocarbonyl C1 to C6 alkyl which may be substituted include phenylaminocarbonylmethyl, 1-phenylaminocarbonylethyl and the like, and examples of the phenyl C1 to C4 alkylaminocarbonyl C1 to C6 alkyl which may be substituted include benzylaminocarbonylmethyl, 1-benzylaminocarbonylethyl and the like,
examples of the C1 to C6 alkyl represented by R9 include methyl, ethyl, propyl, isopropyl, butyl and the like, and
the halogen represented by X1 and X2 means fluorine, chlorine, bromine or iodine.
In the present compounds, from the standpoint of herbicidal activity, those are preferable wherein Q-R3 is Q-1, Q-2 or Q-6, Y is oxygen or sulfur, more preferably oxygen, R1 is methyl substituted with fluorine (for example, trifluoromethyl, chlorodifluoromethyl, difluoromethyl or the like), or ethyl substituted with fluorine (for example, pentafluoroethyl, 1,1-difluoroethyl or the like), more preferably trifluoromethyl, R2 is methyl or ethyl, more preferably methyl, R3 is C1 to C4 alkoxycarbonyl C1 to C4 alkyl, C1 to C4 alkoxycarbonyl C1 to C4 alkoxy, C3 to C7 cycloalkoxycarbonyl C1 to C4 alkoxy, C1 to C4 alkoxycarbonyl C1 to C4 alkylthio or C1 to C4 alkoxycarbonyl C1 to C4 alkylamino, more preferably C1 to C2 alkoxycarbonyl C1 to C2 alkoxy, X1 is halogen, more preferably chlorine, and/or X2 is halogen, more preferably fluorine.
As the specially prefered compounds, compound wherein Q-R3 is 2-(methoxycarbonyl)methoxy-3-pyridyl, 2-(ethoxycarbonyl)methoxy-3-pyridyl, 4-{1-(methoxycarbonyl)ethoxy}-2-pyrimidyl, R1 is trifluoromethyl, R2 is methyl, X1 is chlorine, X2 is fluorine, and Y is oxygen.
Sometimes, geometrical isomers based on double bond, optical isomers and diastereomers based on asymmetric carbon, may be present in the present compound, and the present compound also includes these isomers and mixtures thereof.
Next, methods for producing the present compounds will be illustrated.
The present compound can be produced, for example, by the following (Production Method 1) to (Production Method 10).
(Production Method 1)
Of the present compounds, the compound [I] wherein R3 is OR7, SR8 or N(R9)R10 can be produced by reacting a compound [III] of the formula [III]
[wherein, R1, R2, Y, Q, X1 and X2 are the same as defined above, and W represents oxygen, sulfur, imino or, C1 to C3 alkylimino such as methylimino and the like.]
with a compound [IV] of the formula [IV]
R11xe2x80x94R12xe2x80x83xe2x80x83[IV]
[wherein, R11 represents carboxy C1 to C6 alkyl, C1 to C6 alkoxycarbonyl C1 to C6 alkyl, C1 to C6 haloalkoxycarbonyl C1 to C6 alkyl, C3 to C6 alkenyloxycarbonyl C1 to C6 alkyl, C3 to C6 alkynyloxycarbonyl C1 to C6 alkyl, phenoxycarbonyl C1 to C6 alkyl which may be substituted, phenyl C1 to C4 alkoxycarbonyl C1 to C6 alkyl which may be substituted, C1 to C6 alkoxyaminocarbonyl C1 to C6 alkyl, (C1 to C6 alkoxy)(C1 to C3 alkyl)aminocarbonyl C1 to C6 alkyl, C1 to C6 alkylaminocarbonyl C1 to C6 alkyl, (C1 to C6 alkyl) C1 to C6 alkylaminocarbonyl C1 to C6 alkyl, phenylaminocarbonyl C1 to C6 alkyl which may be substituted, or phenyl C1 to C4 alkylaminocarbonyl C1 to C6 alkyl which may be substituted, and R12 represents a leaving group such as chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like.]
in the presence of a base.
This reaction is usually conducted in a solvent, and the reaction temperature is usually in a range from 0 to 200xc2x0 C., and the reaction time is usually in a range from instant to 72 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [IV] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [III], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, quinoline, benzyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,4-diazabicyclo[2.2.2]octane, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, diisopropylethylamine and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl formate, ethyl acetate, butyl acetate, diethyl carbonate and the like, nitro compounds such as nitromethane, nitrobenzene and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethyl sulfoxide, sulfolane and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The resulted present compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Production Method 2)
Of the present compounds, the compound [I] wherein R3 is OR7 can be produced by reacting a compound [V] of the formula [V]
[wherein, R1, R2, Y, Q, X1 and X2 are the same as defined above.]
with an alcohol compound [VI] of the formula [VI]
R7xe2x80x94OHxe2x80x83xe2x80x83[VI]
[wherein, R7 is the same as defined above.]
in the presence of a dehydrating reagent.
This reaction is usually conducted in a solvent, and the reaction temperature is usually in a range from xe2x88x9220 to 150xc2x0 C., preferably from 0 to 100xc2x0 C., and the reaction time is usually in a range from instant to 48 hours.
As the dehydrating reagent, there are listed, for example, combinations of triarylphosphine such as triphenylphosphine and the like, and di(lower alkyl)azodicarboxylate such as diethyl azodicarboxylate, diisopropyl azodicarboxylate and the like.
Regarding the amounts of reagents to be reacted, the amount of the alcohol compound [VI] is from 1 to 3 mol, preferably from 1 to 1.5 mol, the amount of the triarylphosphine used as a dehydrating agent is from 1 to 3 mol, preferably from 1 to 1.5 mol, and the amount of a di(lower alkyl)azodicarboxylate is from 1 to 3 mol, preferably from 1 to 1.5 mol, based on 1 mol of the compound [V]. The ratio of these reagents can be optionally changed depending on reaction conditions.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as toluene, xylene and the like, halogenated aromatic hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, diisopropyl ether, dioxane, THF, ethylene glycol dimethyl ether, and the like, esters such as ethyl acetate and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated, and the residue is subjected to chromatography.
2) The reaction solution is concentrated as it is, and the residue is subjected to chromatography.
The resulted present compound can also be purified by an operation such as re-crystallization and the like, in some cases.
(Production Method 3)
Of the present compounds, some compounds can be produced by using a carboxylic acid compound [VII] of the formula [VII]
[wherein, R1, R2, Y, Q, X1, X2and W are the same as defined above, R13 represents C1 to C6 alkylidene or C2 to C6 alkylene and m represents an integer of 0 or 1.]
and an alcohol compound [VIII] of the formula [VIII]
HOxe2x80x94R14xe2x80x83xe2x80x83[VIII]
[wherein, R14 represents C1 to C6 alkyl, C1 to C6 haloalkyl, C3 to C6 alkenyl, C3 to C6 haloalkenyl, C3 to C6 alkynyl or C3 to C6 haloalkynyl.]
as raw materials.
This reaction is conducted, for example, by reacting the carboxylic acid compound [VII] with a chlorinating agent to give an acid chloride (hereinafter, referred to as  less than Process 3-1 greater than ), then, reacting the acid chloride with the alcohol compound [VIII] in the presence of a base (hereinafter, referred to as  less than Process 3-2 greater than ).
 less than Process 3-1 greater than  is conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from 0 to 150xc2x0 C. and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the chlorinating agent is 1 mol based on 1 mol of the carboxylic acid compound [VII], however, the ratio can be optionally changed depending on reaction conditions.
As the chlorinating agent used, there are listed, for example, thionyl chloride, sulfuryl chloride, phosgene, oxalyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, nonane, decane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene and the like, aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2,3-trichloropropane and the like, aliphatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, esters such as ethyl acetate and the like, or mixtures thereof.
After completion of the reaction, for example, the reaction solution is concentrated, and the concentrated residue is used as it is in  less than Process 3-2 greater than .
 less than Process 3-2 greater than is conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from xe2x88x9220 to 100xc2x0 C. and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amounts of the alcohol compound [VIII] and the base are 1 mol, respectively, based on 1 mol of the carboxylic acid compound [VII] used in  less than Process 3-1 greater than , however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed, for example, inorganic bases such as sodium hydrogen carbonate, potassium hydrogen carbonate, lithium carbonate, sodium carbonate, potassium carbonate and the like, nitrogen-containing aromatic compounds such as pyridine, quinoline, 4-dimethylaminopyridine, 2-picoline, 3-picoline, 4-picoline, 2,3-lutidine, 2,4-lutidine, 2,5-lutidine, 2,6-lutidine, 3,4-lutidine, 3,5-lutidine, 3-chloropyridine, 2-ethyl-3-ethylpydirine, 5-ethyl-2-methylpydirine and the like, and tertiary amines such as triethylamine, diisopropylethylamine, tri-n-propylamine, tri-n-butylamine, benzyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,4-diazabicyclo[2.2.2]octane and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, nonane, decane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene and the like, aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2,3-trichloropropane and the like, aromatic halogenated hydrocarbons such as monochlorobenzene, dichlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, esters such as ethyl acetate and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The resulted present compound can also be purified by an operation such as chromatography, re-crystallization and the like.
This reaction can also be conducted by reacting the compound [VII] with the compound [VIII] in the presence of a condensing agent with a base or without a base in a solvent. The reaction temperature is usually in a range from 0 to 100xc2x0 C., and the reaction time is usually in a range from instant to 48 hours.
As the condensing reagent, carbonyldiimidazole, dicyclohexylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and the like, are listed.
As the base, organic bases such as triethylamine, diisopropylethylamine and the like, are listed.
Regarding the amounts of reagents to be reacted, the amount of the compound [VIII] is from 1 to 3 mol, the amount of the condensing reagent is from 1 to 3 mol, the amount of the base is from 0.5 to 3 mol, based on 1 mol of the compound [VII]. The ratio of these reagents can be optionally changed depending on reaction conditions.
As the solvent used, dichloromethane, amide such as N,N-dimethylformamide, ethers such as tetrahydrofuran, and the like, or mixtures thereof are listed.
After completion of the reaction, an intended present compound can be obtained, for example, by the reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. The resulted present compound can also be purified by an operation such as chromatography, re-crystallization and the like.
Further, this reaction can also be conducted by a method in which a reaction is conducted in the presence of an acid catalyst, an other known methods, in addition to the above-mentioned methods.
(Production Method 4)
Of the present compounds, the compound [I] wherein X1 is cyano can be produced by reacting a uracil compound [IX] of the formula [IX]
[wherein, R1, R2 and X2 are the same as defined above, and R15 represents fluorine, chlorine, bromine or iodine.]
with a compound [X] of the formula [X]
[wherein, Y, Q and R3 are the same as defined above.]
in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from 0 to 200xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [X] is 1 mol and the amount of the base is 1 mol based on 1 mol of the uracil compound [IX], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, and the like, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, or mixtures thereof.
This reaction may sometimes be accelerated by using a catalyst. As the catalyst, copper iodide, copper bromide, copper chloride, copper powder and the like are listed, and the amount of the catalyst to be used in the reaction is from 0.0001 to 1 mol based on 1 mol of the uracil compound [IX], and this ratio can be optionally changed depending on conditions of the reaction.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The resulted present compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Production Method 5)
The present compound can be produced by reacting a uracil compound [XI] of the formula [XI]
[wherein, R1, R2, Y, X1 and X2 are the same as defined above.]
with a compound [XII] of the formula [XII]
[wherein, R16 represents a leaving group such as fluorine, chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like, and R3 is the same as defined above.]
in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from room temperature to 200xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XII] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XI], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, and the like, nitrites such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, or mixtures thereof.
This reaction may sometimes be accelerated by using a catalyst.
The amount of the catalyst to be used in the reaction is preferably from 0.0001 to 1 mol based on 1 mol of the compound [XI], and this ratio can be optionally changed depending on conditions of the reaction.
As the catalyst, there are listed copper compounds such as copper iodide, copper bromine, copper chloride, copper powder and the like, and crown ethers such as 12-crown-4, 15-crown-5, 18-crown-6 and the like.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Production Method 6)
The present compound can be produced by reacting a uracil compound [XXXI] of the formula [XXXI]
[wherein, R1, R3, Y, Q, X1 and X2 are the same as defined above.]
with a compound [XXXX] of the formula [XXXX]
R12xe2x80x94R2xe2x80x83xe2x80x83[XXXX]
[wherein, R2 and R12 are the same as defined above.]
in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from xe2x88x9220 to 150xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XXXX] is 1 mol and the amount of the base is 1 mol based on 1 mol of the uracil compound [XXXI], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, quinoline, benzyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,4-diazabicyclo[2.2.2]octane, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, diisopropylethylamine and the like, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, and the like, nitro compounds such as nitromethane, nitrobenzene and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, alcohols such as methanol, ethanol, ethylene glycol, isopropanol, t-butanol and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1), 2) or 3).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction mixture is poured into water and the precipitate is collected by filtration.
3) A reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The resulted present compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Production Method 7)
Of the present compounds, the compound [I] wherein Q is a pyrazolediyl group can be produced by a method shown in the following scheme. 
[wherein, R1, R2, R11, R12, X1 and X2 are the same as defined above. R20 represents lower alkyl such as methyl, ethyl and the like, R21 represents hydrogen, C1 to C6 alkyl, C2 to C6 alkenyl or C2 to C6 alkynyl, R22 represents C1 to C6 alkyl, C2 to C6 alkenyl or C2 to C6 alkynyl, and Y1 represents oxygen, sulfur or alkylimino.].
 less than Step a greater than : A process to produce the compound [XXXIII] from the compound [XXXII].
The compound [XXXIII] can be produced by reacting the compound [XXXII] with the compound [XXXXII] in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from 0 to 150xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XXXXII] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXII], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, metal alkoxides such as sodium methoxide, potassium t-butoxide and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, petroleum ether and the like, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, alcohols such as methanol, ethanol, t-butanol and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Step b greater than : A process to produce the compound [XXXIV] from the compound [XXXIII].
The compound [XXXIV] can be produced by reacting the compound [XXXIII] with a formylating agent in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from 0 to 100xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the formulating agent is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXIII], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide and the like, and inorganic bases such as sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Step c (R21 in not hydrogen( greater than : A process to produce the compound [XXXIV] from the compound [XXXII].
The compound [XXXIV] can be produced by reacting the compound [XXXII] with the compound [XXXXIII] in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from 0 to 150xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XXXXIII] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXII], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, quinoline, benzyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, N, N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, metal alkoxides such as potassium t-butoxide and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, sodium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, petroleum ether and the like, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Step d greater than : A process to produce the compound [XXXV] from the compound [XXXIV].
The compound [XXXV] can be produced, for example, by reacting the compound [XXXIV] with a hydrazine compound in a solvent.
The reaction temperature is in a range from 0 to 200xc2x0 C., preferably from room temperature to reflux temperature. The reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical the amount of the hydrazine compound is 1 mol based on 1 mol of the compound [XXXIV], however, the ratio can be optionally changed depending on reaction conditions.
As the hydrazine compound used, there are listed hydrazine monohydrate, methyl carbazate and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, petroleum ether and the like, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, alcohol such as methanol, ethanol and the like.
The reaction solution after completion of the reaction can be poured into water and the precipitated crystals are collected by filtration, or subjected to usual post treatments such as extraction with an organic solvent, neutralization, concentration and the like, to obtain an intended compound.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Step e greater than : A process to produce the compound [XXXVI] from the compound [XXXV].
The compound [XXXVI] can be produced by reacting the compound [XXXV] A) with the compound [IV] in the presence of a base, or B) with the alcohol compound [VI] in the presence of a dehydrating agent.
A) This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is in a range from 0 to 200xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [IV] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXV], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, benzyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, metal alkoxides such as sodium methoxide, potassium t-butoxide and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, butyl acetate, and the like, nitro compounds such as nitromethane, nitrobenzene and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, alcohols such as methanol, ethanol, ethylene glycol, isopropanol, t-butanol and the like, or mixtures thereof.
After completion of the reaction, an intended compound can be obtained, for example, by pouring the reaction solution into water, extracting this with an organic solvent, and drying and concentrating the organic layer.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
B) The reaction is usually conducted in a solvent, and the reaction temperature is usually in a range from xe2x88x9220 to 150xc2x0 C., preferably from 0 to 100xc2x0 C., and the reaction time is usually in a range from instant to 48 hours.
As the dehydrating reagent, there are listed, for example, combinations of triarylphosphine such as triphenylphosphine and the like, and di(lower alkyl)azodicarboxylate such as diethyl azodicarboxylate, diisopropyl azodicarboxylate and the like.
Regarding the amounts of reagents to be reacted, the amount of the alcohol compound [VI] is from 1 to 3 mol, preferably from 1 to 1.5 mol, the amount of the triarylphosphine used as a dehydrating agent is from 1 to 3 mol, preferably from 1 to 1.5 mol, and the amount of the di(lower alkyl)azodicarboxylate is from 1 to 3 mol, preferably from 1 to 1.5 mol, based on 1 mol of the compound [XXXV]. The ratio of these reagents can be optionally changed depending on reaction conditions.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as benzene, toluene, xylene and the like, halogenated aromatic hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, diisopropyl ether, dioxane, THF, ethylene glycol dimethyl ether, diglyme and the like, esters such as ethyl acetate and the like, or mixtures thereof.
After completion of the reaction, an intended compound can be obtained by subjecting the reaction solution to usual post treatments such as addition of water and then extraction with an organic solvent, concentration and the like.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Step f greater than : A process to produce the compound [XXXVII] from the compound [XXXVI],
The compound [XXXVII] can be produced by reacting the compound [XXXVI] with a compound [XXXXIV] of the formula [XXXXIV]
R22xe2x80x94R12xe2x80x83xe2x80x83[XXXXIV]
[wherein, R12 and R22 are the same as defined above.]
in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is in a range from 0 to 200xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XXXXIV] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXVI], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-ene, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like.
As the solvent used, there are listed, for example, aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide, sulfolane and the like, alcohols such as methanol, ethanol, ethylene glycol,=t-butanol and the like, or mixtures thereof.
After completion of the reaction, an intended compound can be obtained by by pouring the reaction solution into water and collecting the precipitated crystals by filtration, or by pouring the reaction solution into water, then, subjecting the mixture to usual post treatments such as extraction with an organic solvent, concentration and the like.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Production Method 8)
The present compound can be produced by a method shown in the following scheme. 
[wherein, R1, R2, R11, W, Y, Q, X1 and X2 are the same as defined above, Axe2x88x92 represents counter anion of diazonium ion such as Clxe2x88x92, BF4xe2x88x92, CF3SO3xe2x88x92 and the like.].
 less than Step 8-1 greater than : A process to produce the compound [XXXXVI] from the compound [XXIII].
The compound [XXXXVI] can be produced, for example, by reacting the compound [XXIII] with a diazotizing agent and an acid in a solvent.
The reaction temperature is from xe2x88x9230 to 30xc2x0 C., and the reaction time is usually from an instant to 10 hours.
Regarding the amounts of reagents to be reacted, the amount of the diazotizing agent is from 1 mol to 3 mol, and the amount of the acid is from 1 mol to 6 mol based on 1 mol of the compound [XXIII], however, the ratio can be optionally changed depending on the reaction conditions.
diazotizing agent: nitrites such as sodium nitrite, isoamyl nitrite, t-butyl nitrite and the like
acid: inorganic acids such as tetrafluoroboric acid, hydrochloric acid and the like, organic acids such as trifluoromethanesulfonic acid and the like, lewis acid such as boron trifluoride diethyl etherate and the like.
solvent: aliphatic halogenated hydrocarbons such as methylene chloride, chloroform 1,2-dichloroethane, 1,2, 3-trichloropropane and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and the like, aqueous hydrochloric acid solution, aqueous hydrobromic acid solution, aqueous sulfuric acid solution and the like, or mixtures thereof.
After completion of the reaction, the reaction solution is used in the subsequent reaction as it is, or nonpolar organic solvent such as n-pentane, n-hexane and the like is added to the reaction solution and the precipitate is collected by filtration, for example.
 less than Step 8-2 greater than : A process to produce the compound [XIV] from the compound [XXXXVI].
The compound [XIV] can be produced, for example, by reacting the diazonium salt compound [XXXXVI] with the compound [XIII] in a solvent.
The reaction temperature is from 0 to 120xc2x0 C., and the reaction time is usually from an instant to 20 hours.
Regarding the amounts of reagents to be reacted, the amount of the compound [XIII] is from 1 mol to 10 mol based on 1 mol of the compound [XXXXVI], however, the ratio can be optionally changed depending on the reaction conditions.
solvent: aromatic hydrocarbons such as toluene and the like, aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane and the like, ethers such as diethyl ether, tetrahydrofuran, ethylene glycol dimethyl ether and the like, or mixtures thereof.
After completion of the reaction, the intended present compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
Further, the resulted present compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
(Production Method 9)
Of the present compounds, the compound [I] wherein X1 is nitro (compound [XVI]) or halogen (compound [XVIII]) can be produced by a method shown in the following scheme. 
[wherein, R1, R2, R3, R15, Q, Y and X2 are the same as defined above, and R25 represents fluorine, chlorine, bromine or iodine.].
 less than Process 9-1 greater than : The compound [XVI] can be produced, for example, by reacting the compound [XV] with the compound [X] in the presence of a base.
This reaction is conducted usually without a solvent or in a solvent, and the reaction temperature is from 0 to 200xc2x0 C., and the reaction time is usually from an instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [X] is 1 mol and the amount of the base is 1 mol based on 1 mol of the uracil compound [XV], however,the ratio can be optionally changed depending on the reaction conditions.
The base to be used includes organic bases such as pyridine, quinoline, benzyldimethylamine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]undec-7-en, 1,5-diazabicyclo[4.3.0]non-5-ene, 1,4-diazabicyclo[2.2.2]octane, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, diisopropylethylamine and the like, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide and the like, and inorganic bases such as lithium carbonate, sodium carbonate, potassium carbonate, calcium carbonate, barium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide and the like.
Examples of the solvent to be used include aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin, cyclohexane, petroleum ether and the like; aromatic hydrocarbons such as benzene, toluene, xylene and the like; aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like; ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like; ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; nitriles such as acetonitrile, isobutyronitrile and the like; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidinone and the like; sulfur compounds such as dimethyl sulfoxide, sulfolane and the like; alcohols such as methanol, ethanol, ethylene glycol, isopropanol, t-butanol and the like; or mixtures thereof.
After completion of the reaction, the intended present compound can be obtained, for example, by the following operation 1), 2) or 3).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction mixture is poured into water and the precipitate is collected by filtration.
3) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
Further, the resulted present compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Process 9-2 greater than : The compound [XVII] can be produced, for example, by reducing the compound [XVI] in a solvent, A) using an iron powder in the presence of an acid, B) with hydrogen in the presence of a catalyst.
A) This reaction is conducted usually in a solvent, and the reaction temperature is usually from 0 to 150xc2x0 C., preferably from room temperature to the reflux temperature. The reaction time is usually from an instant to 24 hours.
Regarding the amounts of reagents to be used in the reaction, the amount of the iron powder is from 3 mol to excess and the amount of the acid is 1 to 10 mol based on 1 mol of the compound [XVI], however, the ratio can be optionally changed depending on the reaction conditions.
As the acid to be used, acetic acid and the like are listed.
As the solvent to be used, there are listed, for example, water, aceti c acid, ethyl acetate and the like or mixtures thereof.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as by filtrating, then, pouring a reaction solution into water and the deposited crystals are collected by filtration, or, extracting with an organic solvent, neutralization, drying, concentration and the like.
B) This reaction is usually conducted in a solvent, the reaction temperature is usually from xe2x88x9220 to 150xc2x0 C., preferably from 0 to 50xc2x0 C. The reaction time is usually from an instant to 48 hours.
This reaction can also be conducted under pressure, and the reaction is preferably conducted under a pressure of 1 to 5 atom.
The amount of the catalyst used in this reaction is from 0.001 to 10% by weight based on the compound [XVI].
As the catalyst to be used in the reaction, anhydrous palladium/carbon, water-containing palladium/carbon, platinum oxide and the like are listed.
The solvent includes carboxylic acids such as formic acid, acetic acid, propionic acid and the like, esters such as ethyl formate, ethyl acetate, butyl acetate and the like, ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and the like, alcohols such as methanol, ethanol and the like, or mixtures thereof and the like.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating a reaction solution before concentrating the solution itself, and the like.
The intended material can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Process 9-3 greater than : The compound [XVIII] can be produced from the compound [XVII], for example, A) by i) diazotizing the compound [XVII] in a solvent, then, ii) subsequently reacting it with halogenating agent in a solvent.
B) by reacting the compound [XVII] with a diazotizing agent in a solvent in the presence of halogenating agent. (see, Heterocycles., 38, 1581 (1994) and the like)
A)i) In the diazotization reaction of the first step, the reaction temperature is usually from xe2x88x9220 to 10xc2x0 C., and the reaction time is usually from an instant to 5 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the diazotizing agent is 1 mol based on 1 mol of the compound [XVII], however, the ratio can be optionally changed depending on the reaction conditions.
As the diazotizing agent to be used, nitrites such as sodium nitrite, potassium nitrite, isoamyl nitrite, t-butyl nitrite and the like, are listed.
As the solvent to be used, there are listed, for example, acetonitrile, hydrobromic acid, hydrochloric acid, sulfuric acid, water and the like or mixtures thereof.
The reaction solution after completion of the reaction is used as it is in the following reaction.
ii) In the reaction of the second step, the reaction temperature is usually in a range from 0 to 80xc2x0 C., and the reaction time is usually in a range from an instant to 48 hours.
Regarding the amounts of reagents to be used in the reaction, halogenating agent is from 1 to 3 mol based on 1 mol of the compound [XVII], and the amounts thereof can be optionally changed depending on the reaction condition.
As the halogenating agent used, potassium iodide, copper(I) bromide (or mixture with copper(II) bromide), copper(I) chloride (or mixture with copper(II) chloride) or a mixture of hydrofluoric acid and boric acid (hereinafter, referred to as hydroborofluoric acid) and the like are listed.
As the solvent to be used, there are listed, for example, acetonitrile, diethyl ether, hydrobromic acid, hydrochloric acid, sulfuric acid, water and the like or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following treatment; reaction solution is poured into water and if necessary acid such as hydrochloric acid, this is extracted with an organic solvent, and the resulted organic layer is dried and concentrated.
(see, Org. Syn. Coll. Vol. 2, 604 (1943), Vol. 1, 136 (1932))
B) the reaction temperature is usually from xe2x88x9220 to 50xc2x0 C., preferably from xe2x88x9210xc2x0 C. to room temperaature, and the reaction time is usually from an instant to 48 hours.
Regarding the amounts of reagents to be reacted, the amount of the the halogenating agent is from 1 mol to 3 mol, the amount of the diazotizing agent is from 1 mol to 3 mol respectively, based on 1 mol of the compound [XVII], however, the ratio can be optionally changed depending on the reaction conditions.
As the halogenating agent used, for example, iodine, copper(I) bromide (or mixture with copper(II) bromide), copper(I) chloride (or mixture with copper(II) chloride) or hydroborofluoric acid and the like are listed.
As the diazotizing agent to be used, nitrites such as isoamyl nitrite, t-butyl nitrite and the like, are listed.
As the solvent to be used, there are listed, for example, acetonitrile, benzene, toluene and the like or mixtures thereof.
After completion of the reaction, an intended present compound can be obtained, for example, by the following treatment; the reaction solution is poured into water, and added if necessary acid such as hydrochloric acid, then, this is extracted with an organic solvent, and the resulted organic layer is dried and concentrated.
Further, the resulted present compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
(Production Method 10)
Of the present compounds, the compound [I] wherein X1 is cyano (compound [10-3]) can be produced by a method shown in the following scheme. 
Wherein R1, R2, R3, Q, X2 and Y are the same as defined above, X10 is bromine or iodine, and M1 represents metal such as copper, potassium, sodium, and the like.
The compound [10-3] can be produced by reacting the compound [10-1] with the compound [10-2].
This reaction is usually carried out in a solvent. The reaction temperature is usually in a range from 130 to 250xc2x0 C., preferably 150xc2x0 C. to reflux temperature and the reaction time is usually from an instant to 24 hours.
The compound [10-2] used in the reaction includes copper cyanide, potassium cyanide, sodium cyanide and the like.
The amount of the compound [10-2] is in a ratio from 1 mole to excess amount, preferably from 1 to 3 mole based on 1 mole of the compound[10-1], however, the ratio can be optionally changed depending on the reaction conditions.
Examples of the solvent to be used include ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-2-pyrrolidone and the like; sulfur compounds such as dimethyl sulfoxide, sulfolane and the like; or mixtures thereof.
After completion of the reaction, an objected compound can be obtained, for example, by subjecting to the ordinary after treatment by the following procedure.
1) The reaction mixture is filtered and concentrated.
2) The reaction mixture is added to water, extracted with an organic solvent, washed with water, dried and concentrated.
Further, the object compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
The compound [IV], alcohol compound [VI], alcohol compound [VIII], compound [X], compound [XIII], compound [XV], compound [XXXX], compound [XXXXII], compound [XXXXIII], compound [XXXXIV] used in the production methods of the present compound are commercially available, or can be produced by known methods.
The compound [IX] is known, for example, from DE4412079 A.
The carboxylic acid compound [VII] can be produced by acidolyzing the present compound [I] wherein the corresponding site is an ester.
The compound [XI] is known, for example, from JP-A Nos. 63-41466, 61-40261 and WO9847904, or can be produced according to methods in these publications.
Some production intermediates used in the production methods of the present compound can be produced, for example, by the following (Intermediate Production Method 1) to (Intermediate Production Method 12).
(Intermediate Production Method 1)
Compound [XII] wherein R3 is OR7, SR8 or N(R9)R10 can be produced by a method shown in the following scheme. 
[wherein, R26 represents a leaving group such as fluorine, chlorine, bromine, iodine, methanesulfonyloxy, p-toluenesulfonyloxy and the like, R11, R16, Q and W are the same as defined above.].
The compound [X1-2] can be produced, for example, by reacting the compound [X1-1] with the compound [XIII]in a solvent, in the presence of a base.
This reaction condition, for example, is as follows.
Reaction temperature: from 0 to 180xc2x0 C.
Reaction time: from an instant to 24 hours
The amount of the compound [XIII]: from 1 mol to 1.5 mol based on 1 mol of the compound [X1-1]
The amount of the base : from 1 mol to 1.5 mol based on 1 mol of the compound [X1-1]
However, the ratio can be optionally changed depending on the reaction conditions.
Base: triethylamine, diisopropylethylamine, potassium carbonate, sodium hydride and the like
Solvent: dioxane, tetrahydrofuran, N,N-dimethylformamide, 1-methyl-2-pyrrolidinone and the like
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography and the like.
(Intermediate Production Method 2)
Compound [III] wherein W is NH (compound [XXIII]) can be produced by a method shown in the following scheme. 
[wherein, R1, R2, R16, Y, Q, X1 and X2 have the same meanings as described above.].
 less than Process A2-1 greater than : A process to produce the compound [XXII] from the compound [XI].
The compound [XXII] can be produced by reacting the compound [XI] with the compound [XXI] in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is in a range from 0 to 200xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XXI] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XI], however, the ratio can be optionally changed depending on reaction conditions.
Base: triethylamine, diisopropylethylamine, potassium carbonate, sodium hydride, sodium hydroxide and the like
Solvent: toluene, dioxane, tetrahydrofuran, N,N-dimethylformamide, 1-methyl-2-pyrrolidinone, dimethylsulfoxide, sulfolane and the like, or mixtures thereof.
This reaction may sometimes be accelerated by addition of a catalyst.
The preferrable amount of the catalyst to be used in the reaction is from 0.0001 to 0.1 mol based on 1 mol of the compound [XI], and this ratio can be optionally changed depending on conditions of the reaction.
As the catalyst, copper compounds such as copper iodide, copper bromide, copper chloride, copper powder and the like, and crown ethers such as 15-crown-5, 18-crown-6 and the like, are listed.
After completion of the reaction, an intended compound can be obtained, for example, by the following treatment; the reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
An intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Process A2-2 greater than : A process to produce the compound [XXIII] from the compound [XXII].
The compound [XXIII] can be produced, for example, by reducing the compound [XXII] in a solvent, A) using an iron powder in the presence of an acid, B) with hydrogen in the presence of a catalyst.
A) The reaction temperature is usually from 0 to 150xc2x0 C., preferably from room temperature to the reflux temperature. The reaction time is usually from an instant to 24 hours.
Regarding the amounts of reagents to be used in the reaction, the amount of the iron powder is from 3 mol to excess and the amount of the acid is 1 to 10 mol based on 1 mol of the compound [XXII], however, the ratio can be optionally changed depending on the reaction conditions.
As the acid to be used, acetic acid and the like are listed.
As the solvent to be used, there are listed, for example, water, acetic acid, ethyl acetate and the like or mixtures thereof.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating, then, pouring a reaction solution into water and collecting the deposited crystals by filtration, or, extracting with an organic solvent, neutralization, drying, concentration and the like.
B) The reaction temperature is usually from xe2x88x9220 to 150xc2x0 C., preferably from 0 to 50xc2x0 C. The reaction time is usually from an instant to 48 hours.
This hydrogenation reaction can also be conducted under pressure, and the reaction is preferably conducted under a pressure of 1 to 5 atom.
The amount of the catalyst used in this reaction is from 0.01 to 10% by weight based on the compound [XXII].
As the catalyst to be used in the reaction, palladium/carbon, platinum oxide and the like are listed.
The solvent includes acetic acid, ethyl acetate, methanol, ethanol and the like, or mixtures thereof.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating a reaction solution before concentrating the solution itself, and the like.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Intermediate Production Method 3)
Compounds [III] wherein W is oxygen (compound [V]) can be produced by a method shown in the following scheme. 
[wherein, R1, R2, Y, Q, X1 and X2 are the same as defined above.].
The compound [V] can be produced by i) reacting the compound [XXIII] with a diazotizing agent in a solvent, in the presence or absence of an acid, then, ii) subsequently, heating the reaction product in an acidic solvent or allowing a copper salt to act on the reaction product in the presence or absence of a copper catalyst.
i) In the reaction of the first step, the reaction temperature is in a range from xe2x88x9220 to 10xc2x0 C. and the reaction time is usually in a range from instant to 5 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the diazotizing agent is 1 mol and the amount of the acid is 1 mol based on 1 mol of the compound [XXIII], however, the ratio can be optionally changed depending on reaction conditions.
As the diazotizing agent used, there are listed, nitrite such as sodium nitrite, potassium nitrite, isoamyl nitrite, t-butyl nitrite and the like.
As the acid used, there are listed, for example, tetrafluoroboric acid, hydrochloric acid, trifluoromethanesulfonic acid, lewis acid such as boron trifluoride diethyl etherate, and the like.
As the solvent used, there are listed, for example, aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichloroethane, 1,2,3-trichloropropane and the like, ethers such as diethyl ether, diisopropyl ether, methyl-t-butyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diglyme and the like, acetonitrile, aqueous hydrochloric acid solution, aqueous hydrobromic acid solution, aqueous sulfuric acid solution and the like, or mixtures thereof.
The reaction solution after completion of the reaction is used in the subsequent reaction as it is, for example.
ii) In the reaction in which heating is conducted in an acidic solvent, in the second step, the reaction temperature is in a range from 60xc2x0 C. to reflux heating temperature, and the reaction time is usually in a range from instant to 24 hours.
As the acidic solvent, there are listed, for example, aqueous hydrochloric acid solution, aqueous hydrobromic acid solution, aqueous sulfuric acid solution and the like.
After completion of the reaction, an intended material can be obtained, for example, by subjecting the reaction solution to usual post-treatments such as filtrating a reaction solution, extraction with an organic solvent, drying, concentration and the like.
(see, Org. Syn. Coll. Vol. 2, 604 (1943), Vol. 1, 136 (1932))
The reaction in which the copper salt is allowed to act in the presence or absence of the copper catalyst, in the second step, is conducted in a solvent, the reaction temperature is in a range from 0xc2x0 C. to reflux heating temperature, and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, the amount of the copper catalyst is from 0.001 to 5 mol and the amount of the copper salt is from 1 to 100 mol based on 1 mol of the compound [XXIII], however, the ratio can be optionally changed depending on reaction conditions.
As the copper catalyst used, copper(I) oxide and the like are listed, and as the copper salt, copper(II) sulfate, copper(II) nitrate and the like are listed.
As the solvent, water, aqueous hydrochloric acid solution, aqueous sulfuric acid solution, acetic acid and the like, or mixtures thereof, for example, are listed.
After completion of the reaction, an intended compound can be obtained, for example, by subjecting the reaction solution to usual post-treatments such as filtrating a reaction solution, neutralization, extraction with an organic solvent, drying, concentration and the like.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Intermediate Production Method 4)
Compound [X] wherein R3 is OR7 or SR8 (compound [XXVI]) can be produced by a method shown in the following scheme. 
[wherein, R11, R12, Y and Q are the same as defined above, and R17 represents oxygen or sulfur.].
The compound [XXVI] can be produced by reacting the compound [XXV] with the compound [IV] in the presence of a base.
This reaction is usually conducted in a solvent, and the reaction temperature is usually in a range from 0 to 150xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [IV] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXV], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, and inorganic bases such as sodium carbonate, potassium carbonate, sodium hydride, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate and the like, nitriles such as acetonitrile and the like, amides such as N,N-dimethylformamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide and the like, alcohols such as methanol, ethanol and the like, or mixtures thereof.
After completion of the reaction, an intended compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
(Intermediate Production Method 5)
Compound [X] wherein R3 is OR7, SR8 or N(R9)R10, and Y is oxygen or sulfur (compound [XXX]) can be produced by a method shown in the following scheme. 
[wherein, R11, R12, R17, W and Q are the same as defined above, and R19 represents a protective group such as t-butyldimethylsilyl, t-butyl, benzyl, methyl or the like.].
 less than Process A5-l greater than : A process to produce the compound [XXVIII] from the compound [XXVII].
The compound [XXVIII] can be produced by reacting the compound [XXVII] with t-butyldimethylsilyl chloride, isobutene, benzyl chloride, benyzl bromide or the like (see, xe2x80x9cYuki Kagaku Jikken no Tebikixe2x80x9d vol.4, (published by Kagaku Dojin), Protective Groups in Organic Synthesis (published by JOHN WILEY and SONS, INC.)).
 less than Process A5-2 greater than : A process to produce the compound [XXIX] from the compound [XXVIII].
The compound [XXIX] can be produced by reacting the compound [XXVIII] with the compound [IV] in the presence of a base.
This reaction is usually conducted in a solvent, and the reaction temperature is usually in a range from 0 to 150xc2x0 C., and the reaction time is usually in a range from instant to 24 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [IV] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXVIII], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, and inorganic bases such as sodium carbonate, potassium carbonate, sodium hydride, sodium hydroxide, potassium hydroxide, and the like.
As the solvent used, there are listed, for example, aromatic hydrocarbons such as toluene, xylene and the like, aromatic halogenated hydrocarbons such as chlorobenzene, benzotrifluoride and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and the like, ketones such as acetone and the like, esters such as ethyl acetate and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, N-methyl-2-pyrrolidone and the like, sulfur compounds such as dimethylsulfoxide and the like, alcohols such as methanol, ethanol and the like, or mixtures thereof.
After completion of the reaction, an intended compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The intended compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Process A5-3 greater than : A process to produce the compound [XXX] from the compound [XXIX].
The compound [XXX] can be produced by de-protecting the compound [XXIX], for example, according to a method described in xe2x80x9cYuki Kagaku Jikken no Tebiki xe2x80x9d vol. 4, (published by Kagaku Dojin), Protective Groups in Organic Synthesis (published by JOHN WILEY and SONS, INC.).
(Intermediate Production Method 6)
Compound [III] wherein W is oxygen (compound [V]) can be produced by a method shown in the following scheme. 
[wherein, R1, R2, Axe2x88x92, Y, Q, X1 and X2are the same as defined above, R24 represents alkyl such as methyl and the like, or haloalkyl such as trifluoromethyl and the like.].
 less than Step A6-1 greater than : A process to produce the compound [XXXXVIII] from the compound [XXXXVI].
The compound [XXXXVIII] can be produced, for example, by reacting the diazonium salt compound [XXXXVI] with the compound [XXXXVII].
This reaction is usually conducted without a solvent or in a solvent, the reaction temperature is from room temperature to 120xc2x0 C., preferably from 50 to 90xc2x0 C., and the reaction time is usually from an instant to 5 hours.
Regarding the amounts of reagents to be reacted, the amount of the compound [XXXXVII] is from 1 mol to excess based on 1 mol of the compound [XXXXVI], however, the ratio can be optionally changed depending on the reaction conditions.
As the solvent used, acetic acid and the like.
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is concentrated as it is, the residue is diluted with water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Step A6-2 greater than : A process to produce the compound [V] from the compound [XXXXVIII].
The compound [V] can be produced, for example, by reacting the compound [XXXXVIII] in the presence of a base in a solvent.
The reaction temperature is from 0 to 100xc2x0 C., preferably from room temperature to 60xc2x0 C., and the reaction time is usually from 0.5 to 20 hours.
Regarding the amounts of reagents to be reacted, the amount of the base is from 0.1 mol to 10 mol based on 1 mol of the compound [XXXXVIII], however, the ratio can be optionally changed depending on the reaction conditions.
As the base used, there are listed inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and the like.
As the solvent used, for example, there are listed, methanol, ethanol, water and the like, or mixtures thereof.
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is concentrated as it is, the residue is diluted with water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
(Intermediate Production Method 7)
Compound [XXXI] can be produced by a method shown in the following scheme. 
[wherein, R1, R3, R15, Y, Q, X1 and X2 are the same as defined above, and R18 represents lower alkyl such as methyl, ethyl and the like, R27 represents C1 to C6 alkyl such as methyl, ethyl and the like, or phenyl which may be substituted such as phenyl and the like.].
 less than Process A7-1 greater than : A process for producing the compound [XXXXXI] from the compound [XXXXX]
The compound [XXXXXI] can be produced, for example, by reacting the compound [XXXXX] with the compound [X] in the presence of a base.
This reaction is usually conducted without a solvent or in a solvent, and the reaction temperature is usually in a range from 0 to 150xc2x0 C., and the reaction time is usually in a range from instant to 48 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [X] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXXX], however, the ratio can be optionally changed depending on reaction conditions.
As the base used, there are listed organic bases such as pyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide and the like, and inorganic bases such as potassium carbonate, sodium hydrogen carbonate, sodium hydride, lithium hydroxide, sodium hydroxide and the like.
As the solvent used, there are listed, for example, aromatic hydrocarbons such as toluene, xylene and the like, ethers such as dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and the like, ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like, esters such as ethyl acetate, and the like, nitriles such as acetonitrile, isobutyronitrile and the like, amides such as N,N-dimethylformamide, and the like, sulfur compounds such as dimethylsulfoxide and the like, alcohols such as methanol, ethanol and the like, or mixtures thereof.
After completion of the reaction, an intended compound can be obtained, for example, by the following operation 1) or 2).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
The resulted present compound can also be purified by an operation such as chromatography, re-crystallization and the like.
 less than Process A7-2 greater than : A process for producing the compound [XXXXXIII] from the compound [XXXXXI]
The compound [XXXXXIII] can be produced by isocyanating the compound [XXXXXI] in a solvent or without a solvent.
Isocyanating agent: phosgene, trichloromethyl chloroformate, triphosgene, oxalyl chloride and the like.
Amount of isocyanating agent: from 1 mol to excess, preferably from 1.0 to 3 mol based on 1 mol of the compound [XXXXXI].
Solvent: aromatic hydrocarbons such as benzene, toluene and the like, halogenated aromatic hydrocarbons such as chlorobenzene and the like, esters such as ethyl acetate and the like.
Reaction Temperature: from room temperature to reflux temperature.
Reaction Time: from an instant to 48 hours.
This reaction may sometimes be accelerated by adding a catalyst.
The amount of the catalyst used in this reaction is from 0.001 to 300% by weight based on the compound [XXXXXI], and the amounts thereof can be changed optionally depending on the reaction condition.
As the catalyst, charcoal (activated), amines such as triethylamine and the like are listed.
After completion of the reaction, an intended material can be obtained by concentrating a reaction solution itself, and the like. This compound can also be purified by an operation such as re-crystallization and the like.
 less than Process A7-3 greater than : A process for producing the compound [XXXXXII] from the compound [XXXXXI]
The compound [XXXXXII] can be produced by reacting the compound [XXXXXI] with a compound [a7-1] of the formula [a7-1]
[wherein, R27 is the same as defined above, and X12 represents fluorine, chlorine, bromine or iodine.]
in the presence of a base.
This reaction is usually conducted in a solvent, and also can be conducted without a solvent. The reaction temperature is usually from xe2x88x9220 to 200xc2x0 C. The reaction time is usually from an instant to 48 hours.
The amount of the compound [a7-1] used in the reaction is from 0.5 mol to excess, preferably from 1.0 to 1.2 mol based on 1 mol of the compound [XXXXXI].
The amount of the base used in the reaction is from 0.5 mol to excess, preferably from 1.0 to 1.2 mol based on 1 mol of the compound [XXXXXI].
The base includes inorganic bases such as sodium carbonate, sodium hydroxide and the like, organic bases such as pyridine, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like.
The solvent include aliphatic halogenated hydrocarbons such as chloroform and the like, ethers such as tetrahydrofuran, 1,4-dioxane and the like, nitriles such as acetonitrile and the like, esters such as ethyl acetate, water or mixtures thereof, and the like.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating the reaction solution before concentrating the solution itself, or, pouring the reaction solution into water and collecting the produced crystals by filtration, or, pouring the reaction solution into water and subjecting the mixture to extraction with an organic solvent, drying, concentration and the like. This compound can also be purified by an operation such as re-crystallization, chromatography and the like.
 less than Process A7-4 greater than : A process for producing the compound [XXXI] from the compound [XXXXXIII]
The compound [XXXI] can be produced by reacting the compound [XXXXXIII] with the compound [XXXXXIV] in a solvent in the presence of a base.
Amount of the compound [XXXXXIV]: 0.5 mol to excess, preferably from 0.8 to 1.2 mol based on 1 mol of the compound [XXXXXIII].
Base: inorganic bases such as sodium hydride and the like, metal alkoxides such as sodium methoxide, sodium ethoxide and the like.
Amount of a base: 0.5 mol to excess, preferably from 0.8 to 1.2 mol based on 1 mol of the compound [XXXXXIII].
Solvent: aromatic hydrocarbons such as benzene, toluene and the like; halogenated aromatic hydrocarbons such as chlorobenzene and the like; amides such as N,N-dimethylformamide and the like; ethers such as tetrahydrofuran and the like; halogenated aliphatic hydrocarbons such as chloroform and the like; sulfur compounds such as dimethyl sulfoxide and the like; and mixtures thereof
Reaction temperature: xe2x88x9240xc2x0 C. to solvent reflux temperature
Reaction time: instant to 72 hours
After completion of the reaction, an intended material can be obtained by a post-treatment operation such as filtrating a reaction solution before concentrating the solution itself, or, adding an acid to a reaction solution and collecting the produced crystals by filtration, or, adding an acid to a reaction solution, then, subjecting the mixture to extraction with an organic solvent, concentration and the like. As the acid to be added, hydrochloric acid, acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, or aqueous solutions thereof and the like. This compound can also be purified by an operation such as re-crystallization, chromatography and the like.
The resulted compound [XXXI] can also be reacted with the compound [XXXX] according to a method described in (Production Method 6) without conducting the above-mentioned post-treatment, to produce the present compound.
 less than Process A7-5 greater than : A process for producing the compound [XXXI] from the compound [XXXXXII]
The compound [XXXI] can be produced by reacting the compound [XXXXXII] with the compound [XXXXXIV] in the presence of a base.
This reaction is usually conducted in a solvent, and the reaction temperature is usually from xe2x88x9220 to 200xc2x0 C., preferably from 0 to 130xc2x0 C. The reaction time is usually from an instant to 72 hours.
The amount of the compound [XXXXXIV] used in the reaction is from 0.5 mol to excess, preferably from 0.8 to 1.2 mol based on 1 mol of the compound [XXXXXII].
The amount of the base used in the reaction is from 0.5 mol to excess, preferably from 0.8 to 1.2 mol based on the compound [XXXXXII].
The base includes organic bases such as 4-dimethylaminopyridine, diisopropylethylamine and the like, inorganic bases such as sodium carbonate, potassium carbonate, sodium hydride, potassium hydride and the like, metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide and the like.
The solvent includes ketones such as acetone, methyl isobutyl ketone and the like; aliphatic hydrocarbons such as hexane, heptane, petroleum ether and the like; aromatic hydrocarbons such as benzene, toluene, ethylbenzene, xylene, mesitylene and the like; ethers such as diethyl ether, diisopropyl ether, 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, methyl-t-butyl ether and the like; acid amides such as N,N-dimethylformamide, N,N-dimethylacetamide and the like; tertiary amines such as pyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like; sulfur compounds such as dimethylsulfoxide, sulfolane and the like; or mixtures thereof and the like.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating the reaction solution before concentrating the solution itself, or, adding an acid to the reaction solution and collecting the produced crystals by filtration, or, adding an acid to the reaction solution, then, subjecting the mixture to extraction with an organic solvent, concentration and the like. As the acid to be added, there are listed hydrochloric acid, acetic acid, trifluoroacetic acid, p-toluenesulfonic acid, or aqueous solutions thereof and the like. This compound can also be purified by an operation such as re-crystallization, chromatography and the like.
The resulted compound [XXXI] can also be reacted with the compound [XXXX] according to the method described in (Production Method 6) without conducting the above-mentioned post-treatment, to produce the present compound.
(Intermediate Production Method 8)
Compound [X] wherein Y is oxygen, Q is a pyridine ring, and R3 is OR7, SR8 or N(R9)R10 (compound [XXXXXX]) can be produced by a method shown in the following scheme. 
[wherein, R11, R12, R24, Z1, Z2, W and Axe2x88x92 are the same as defined above.].
 less than Step A8-1 greater than : The compound [XXXXXVI] can be produced, for example, by reacting the compound [XXXXXV] with the compound [XIII] in the presence of a base.
This reaction is conducted usually without a solvent or in a solvent, and the reaction temperature is from 0 to 200xc2x0 C., and the reaction time is usually from an instant to 48 hours.
Regarding the amounts of reagents to be reacted, it is theoretical that the amount of the compound [XIII] is 1 mol and the amount of the base is 1 mol based on 1 mol of the compound [XXXXXV], however, the ratio can be optionally changed depending on the reaction conditions.
The base to be used includes organic bases such as pyridine, quinoline, 1,8-diazabicyclo[5.4.0]undec-7-en, 4-dimethylaminopyridine, N,N-dimethylaniline, N,N-diethylaniline, triethylamine, diisopropylethylamine and the like, and inorganic bases such as lithium carbonate, potassium carbonate, sodium hydride, potassium hydride, lithium hydroxide, sodium hydroxide and the like.
Examples of the solvent to be used include aromatic hydrocarbons such as toluene, xylene and the like; aromatic halogenated hydrocarbons such as benzotrifluoride and the like; ethers such tetrahydrofuran, ethylene glycol dimethyl ether and the like; ketones such as acetone, 2-butanone, methyl isobutyl ketone and the like; esters such as ethyl acetate, butyl acetate and the like; nitriles such as acetonitrile, isobutyronitrile and the like; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, 1-methyl-2-pyrrolidinone and the like; sulfur compounds such as dimethyl sulfoxide, sulfolane and the like or mixtures thereof.
After completion of the reaction, the intended compound can be obtained, for example, by the following operation 1), 2) or 3).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction mixture is poured into water and the precipitate is collected by filtration.
3) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
Further, the resulted present compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Step A8-2 greater than : The compound [XXXXXVII] can be produced, for example, by reducing the compound [XXXXXVI] in a solvent, A) using an iron powder in the presence of an acid, B) with hydrogen in the presence of a catalyst.
A) This reaction is conducted usually in a solvent, and the reaction temperature is usually from 0 to 100xc2x0 C., preferably from room temperature to the reflux temperature. The reaction time is usually from an instant to 48 hours.
Regarding the amounts of reagents to be used in the reaction, the amount of the iron powder is from 3 mol to excess and the amount of the acid is 1 to 10 mol based on 1 mol of the compound [XXXXXVI], however, the ratio can be optionally changed depending on the reaction conditions.
As the acid to be used, acetic acid and the like are listed.
As the solvent to be used, there are listed, for example, water, acetic acid, ethyl acetate and the like or mixtures thereof.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating, then, pouring a reaction solution into water and collecting the deposited crystals by filtration, or, extracting with an organic solvent, neutralization, drying, concentration and the like.
B) This reaction is usually conducted in a solvent. The reaction temperature is usually from xe2x88x9220 to 150xc2x0 C., preferably from 0 to 50xc2x0 C. The reaction time is usually from an instant to 48 hours.
This reaction can also be conducted under pressure, and the reaction is preferably conducted under a pressure of 1 to 5 atom.
The amount of the catalyst used in this reaction is from 0.001 to 10% by weight based on the compound [XXXXXVI].
As the catalyst to be used in the reaction, anhydrous palladium/carbon, water-containing palladium/carbon, platinum oxide and the like are listed.
The solvent includes carboxylic acids such as formic acid, acetic acid, propionic acid and the like, esters such as ethyl acetate, butyl acetate and the like, alcohols such as methanol, ethanol and the like, or mixtures thereof and the like.
After completion of the reaction, an intended material can be obtained by a usual post-treatment operation such as filtrating a reaction solution before concentrating the solution itself, and the like.
The intended material can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Step A8-3 greater than : The compound [XXXXXVIII] can be produced, for example, by reacting the compound [XXXXXVII] with a diazotizing agent and an acid in a solvent.
The reaction temperature is from xe2x88x9230 to 30xc2x0 C., and the reaction time is usually from an instant to 5 hours.
Regarding the amounts of reagents to be reacted, the amount of the diazotizing agent is from 1 mol to 3 mol, and the amount of the acid is from 1 mol to 6 mol based on 1 mol of the compound [XXXXXVII], however, the ratio can be optionally changed depending on the reaction conditions.
As the diazotizing agent used, there are listed, for example, nitrites such as sodium nitrite, isoamyl nitrite, t-butyl nitrite and the like.
As the acid used, there are listed, for example, inorganic acids such as tetrafluoroboric acid, hydrochloric acid and the like, organic acids such as trifluoromethanesulfonic acid and the like, lewis acid such as boron trifluoride diethyl etherate and the like.
As the solvent used, there are listed, for example, aliphatic halogenated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, 1,2,3-trichloropropane and the like, ethers such as diethyl ether, dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and the like, or mixtures thereof.
After completion of the reaction, the reaction solution is used in the subsequent reaction as it is, or nonpolar organic solvent such as n-pentane, n-hexane and the like is added to the reaction solution and the precipitate is collected by filtration, for example.
 less than Step A8-4 greater than : The compound [XXXXXIX] can be produced, for example, by reacting the diazonium salt compound [XXXXXVIII] with the compound [XXXXVII].
This reaction is usually conducted without a solvent or in a solvent, the reaction temperature is from room temperature to 120xc2x0 C., preferably from 50 to 90xc2x0 C., and the reaction time is usually from an instant to 5 hours.
Regarding the amounts of reagents to be reacted, the amount of the compound [XXXXVII] is from 1 mol to excess based on 1 mol of the compound [XXXXXVIII], however, the ratio can be optionally changed depending on the reaction conditions.
As the solvent used, acetic acid and the like.
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is concentrated as it is, the residue is diluted with water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Step A8-5 greater than : The compound [XXXXXX] can be produced, for example, by reacting the compound [XXXXXIX] in the presence of a base in a solvent.
The reaction temperature is from 0 to 100xc2x0 C., preferably from room temperature to 60xc2x0 C., and the reaction time is usually from 0.5 to 20 hours.
Regarding the amounts of reagents to be reacted, the amount of the base is from 0.1 mol to 10 mol based on 1 mol of the compound [XXXXXIX], however, the ratio can be optionally changed depending on the reaction conditions.
As the base used, there are listed inorganic bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate and the like.
As the solvent used, for example, there are listed, methanol, ethanol, water and the like, or mixtures thereof.
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is concentrated as it is, the residue is diluted with water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
(Intermediate Production Method 9)
Compound [X] wherein Y is oxygen, Q is a pyrimidine ring, and R3 is OR7, SR8 or N(R9)R10 (compound [I9-4]) can be produced by a method shown in the following scheme. 
[wherein, R11, R19, R25, W and Z1 are the same as defined above.].
 less than Step A9-1 greater than : The compound [I9-2] can be produced, for example, by reacting the compound [I9-1] with a halogenating agent, without a solvent or in a solvent.
Reaction temperature: from 50xc2x0 C. to reflux temperature.
Reaction time: from an instant to 36 hours
halogenating agent: phosphorus oxybromide, phosphorus oxychloride and the like
The amount of the halogenating agent: from 1 mol to excess based on 1 mol of the compound [I9-1]
However,the ratio can be optionally changed depending on the reaction conditions.
Solvent: toluene, and the like
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is concentrated as it is, the residue is diluted with water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
 less than Step A9-2 greater than : The compound [I9-3 ] can be produced, for example, by reacting the compound [I9-2] with the compound [XIII] in a solvent, in the presence of a base.
Reaction temperature: from 0 to 180xc2x0 C.
Reaction time: from an instant to 24 hours
The amount of the compound [XIII]: from 1 mol to 1.5 mol based on 1 mol of the compound [I9-2]
The amount of the base: from 1 mol to 1.5 mol based on 1 mol of the compound [I9-2]
However, the ratio can be optionally changed depending on the reaction conditions.
Base: triethylamine, diisopropylethylamine, potassium carbonate, sodium hydride and the like
Solvent: dioxane, tetrahydrofuran, N,N-dimethylformamide, 1-methyl-2-pyrrolidinone and the like
After completion of the reaction, the intended compound can be obtained, for example, by the following treatment; the reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated. Further, the resulted compound can also be purified by a procedure such as chromatography and the like.
 less than Step A9-3 greater than : The compound [I9-4] can be produced by de-protecting the compound [I9-3], for example, according to a method described in xe2x80x9cYuki Kagaku Jikken no Tebikixe2x80x9d vol. 4, (published by Kagaku Dojin), Protective Groups in Organic Synthesis (published by JOHN WILEY and SONS, INC.).
(Intermediate Production Method 10) 
[wherein, R11, W and Z1 are the same as defined above, and R28 represents chlorine or bromine, R29 represents C1 to C6 alkyl such as methyl, ethyl and the like, or phenyl which may be substituted such as phenyl, 4-methylphenyl and the like, R30 represents C1 to C6 alkyl such as methyl, ethyl and the like, or C1 to C6 haloalkyl such as trifluoromethyl and the like, Y2 represents oxygen or sulfur, n represents 1 or 2.]
(Intermediate Production Method 11)
Compound [XXXXXI] wherein X1 is nitro, fluorine, chlorine, bromine or ioine (compound [I11-5]) can be produced by a method shown in the following scheme. 
[wherein, R3, R15, R25, Y, Q and X2 are the same as defined above. R32 represents C1 to C6 alkyl which may be substituted such as methyl, ethyl, trifluoromethyl, trichloromethyl and the like, and R33 represents nitro, fluorine, chlorine, bromine or iodine.].
(Intermediate Production Method 12)
The compound [XXXI] may be produced by a method described in the following scheme. 
Wherein Q, R1, R3, X1, X2 and Y are the same as defined above.
 less than Process A12-1 greater than : A process for producing compounds [I12-1] from the compound [XXXXXI].
The compound [I12-1] may be produced by reacting the compound [XXXXXI] with the compound [I12-2] of the formula [I12-2]
wherein R1 is the same as defined above, and R31 represents C1 to C6 alkyl such as methyl, ethyl and the like.
The reaction may be carried out without a solvent or in a solvent, and the reaction temperature is usually in a range from room temperature to 150xc2x0 C. or boiling point of the solvent.
The amount of the compound [I12-2] may be 1 to 5 mole based on 1 mole of the compound [XXXXXI].
Examples of the solvent to be used include aliphatic hydrocarbons such as n-hexane, n-heptane, ligroin and the like, aromatic hydrocarbons such as toluene, xylene and the like.
This reaction may be accelerated by using a dealcoholated agent such as molecular sieves 4A and 5A and the like.
After completion of the reaction, an objected compound can be obtained by subjecting to the ordinary after treatment by the following procedure.
1) The reaction mixture is filtered and concentrated.
2) The reaction mixture is poured into water, and the deposited crystals are collected.
3) The reaction mixture is added to acids such as concentrated hydrochloric acid and the like or water, and this is extracted with an organic solvent, and the resulted organic layer is washed with water, dried and concentrated.
Further, the object compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
The compound [I12-1] may be exist as enol isomers and as the hydrate compound [I12-3]
Wherein Q, R1, R3, X1, X2 and Y are the same as defined above, or the mixtures thereof.
 less than Process A12-2 greater than : A process for producing the compound [XXXI] from the compound [I12-1].
The compound [XXXI] can be produced, for example, by reacting the compound [I12-1] with cyanate in the presence of an acid.
The reaction may be carried out without a solvent or in a solvent, and the reaction temperature is usually in a range from 55 to 150xc2x0 C. or boiling point of the solvent, preferably conducted in a range from room temperature to 50xc2x0 C., at first, then in a range from 55 to 150xc2x0 C. or boiling point of the solvent.
The cyanate used includes potassium cyanate and sodium cyanate and the like.
The acid used includes acetic acid, and the like.
The amount of the cyanate used in this reaction is in a ratio from 1 to 10 mole, preferably from 1 to 2 mole based on 1 mole of the compound [I12-1].
The amount of the acids used in this reaction is in a ratio from 1 mole to a large excess amount based on 1 mole of the compound [I12-1].
Examples of the solvent to be used include aliphatic hydrocarbons such as n-hexane, n-heptane and the like, aromatic hydrocarbons such as benzene, toluene, xylene and the like.
After completion of the reaction, an objected compound can be obtained, for example, by the following operation 1), 2) or 3).
1) The reaction solution is poured into water, this is extracted with an organic solvent, and the organic layer is dried and concentrated.
2) The reaction mixture is poured into water and the precipitate is collected by filtration.
3) The reaction solution is concentrated as it is, or, filtrated if necessary, and the filtrate is concentrated.
Further, the object compound can also be purified by a procedure such as chromatography, re-crystallization and the like.
The compounds [XXI], [XXV], [XXVII], [XXXXX], [XXXXXIV] [XXXXXV], [I9-1], [I10-1] and [I11-1] are commercially available, or can be produced by known methods.
The present compounds have excellent herbicidal activity and some of them can exhibit excellent selectivity between crops and weeds. In other words, the present compounds have herbicidal activity against various weeds which may cause some trouble in the foliar treatment and soil treatment on upland fields, such as listed below.
Onagraceous Weeds
large-flowered evening primrose (Oenothera erythrosepala), cutleaf evening primrose (Oenothera laciniata),
Ranunculaceous Weeds
roughseeded buttercup (Ranunculus muricatus), hairy buttercup (Ranunculus sardous)
Polygonaceous Weeds
wild buckwheat (Polygonum convolvulus), pale smartweed (Polygonum lapathifolium), pennsylvania smartweed (Polygonum pensylvanicum), ladysthumb (Polygonum persicaria), curly dock (Rumex crispus), broadleaf dock (Rumex obtusifolius), Japanese knotweed (Polygonum cuspidatum)
Portulacaceous Weeds
common purslane (Portulaca oleracea)
Caryophyllaceous Weeds
common chickweed (Stellaria media), sticky chickweed (Cerastium glomeratum)
Chenopodiaceous Weeds
common lambsquarters (Chenopodium album), kochia (Kochia scoparia)
Amaranthaceous Weeds
redroot pigweed (Amaranthus retroflexus), smooth pigweed (Amaranthus hybridus)
Cruciferous (Brassicaceous) Weeds
wild radish (Raphanus raphanistrum), wild mustard (Sinapis arvensis), shepherdpurse (Capsella bursa-pastoris), virginia pepperweed (Lepidium virginicum)
Leguminous (Fabaceous) Weeds
hemp sesbania (Sesbania exaltata), sicklepod (Cassia obtusifolia), Florida beggarweed (Desmodium tortuosum), white clover (Trifolium repens), common vetch (Vicia sativa), black medik (Medicago lupulina)
Malvaceous Weeds
velvetleaf (Abutilon theophrasti), prickly sida (Sida spinosa)
Violaceous Weeds
field pansy (Viola arvensis), wild pansy (Viola tricolor)
Rubiaceous Weeds
catchweed bedstraw (cleavers) (Galium aparine)
Convolvulaceous Weeds
ivyleaf morningglory (Ipomoea hederacea), tall morningglory (Ipomoea purpurea), entireleaf morningglory (Ipomoea hederacea var. integriuscula), pitted morningglory (Ipomoea lacunosa), field bindweed (Convolvulus arvensis)
Labiate Weeds
red deadnettle (Lamium purpureum), henbit (Lamium amplexicaule)
Solanaceous Weeds
jimsonweed (Datura stramonium), black nightshade (Solanum nigrum)
Scrophulariaceous Weeds
birdseye speedwell (Veronica persica), corn speedwell (Veronica arvensis), ivyleaf speedwell (Veronica hederaefolia)
Composite Weeds
common cocklebur (Xanthium pensylvanicum), common sunflower (Helianthus annuus), wild camomille (Matricaria chamomilla), scentless chamomile (Matricaria perforata or inodora), corn marigold (Chrysanthemum segetum), pineappleweed (Matricaria matricarioides), common ragweed (Ambrosia artemisiufolia), giant ragweed (Ambrosia trifida), horseweed (Erigeron canadensis), Japanese mugwort (Artemisia princeps), tall goldenrod (Solidago altissima), common dandelion (Taraxacum officinale)
Boraginaceous Weeds
forget-me-not (Myosotis arvensis)
Asclepiadaceous Weeds
common milkweed (Asclepias syriaca)
Euphorbiaceous Weeds
sun spurge (Euphorbia helioscopia), spotted spurge (Euphorbia maculata)
Geraniaceous Weeds
Carolina geranium (Geranium carolinianum)
Oxalidaceous Weeds
pink woodsorrel (Oxalis corymbosa)
Cucurbitaceous Weeds
burcucumber (Sicyos angulatus)
Graminaceous Weeds
barnyardgrass (Echinochloa crus-galli), green foxtail (Setaria viridis), giant foxtail (Setaria faberi), large crabgrass (Digitaria sanguinalis), Southern Crabgrass (Digitaria ciliaris), goosegrass (Eleusine indica), annual bluegrass (Poa annua), blackgrass (Alopecurus myosuroides), wild oat (Avena fatua), johnsongrass (Sorghum halepense), quackgrass (Agropyron repens), downy brome (Bromus tectorum), bermudagrass (Cynodon dactylon), fall panicum (Panicum dichotomiflorum), Texas panicum (Panicum texanum), shattercane (Sorghum vulgare), water foxtail (Alopecurus geniculatus)
Commelinaceous Weeds
common dayflower (Commelina communis)
Equisetaceous Weeds
field horsetail (Equisetum arvense)
Cyperaceous Weeds
rice flatsedge (Cyperus iria), purple nutsedge (Cyperus rotundus), yellow nutsedge (Cyperus esculentus)
Furthermore, some of the present compounds exhibit no significant phytotoxicity on the main crops such as corn (Zea mays), wheat (Triticum aestivum), barley (Hordeum vulgare), rice (Oryza sativa), sorghum (Sorghum bicolor), soybean (Glycine max), cotton (Gossypium spp.), sugar beet (Beta vulgaris), peanut (Arachis hypogaea), sunflower (Helianthus annuus), and canola (Brassica napus); horticultural crops such as flowers, ornamental plants, and vegetable crops.
The present compounds can also attain the effective control of various weeds which may cause some trouble in the no-tillage cultivation of soybean (Glycine max), corn (Zea mays), wheat (Triticum aestivum), and other crops. Furthermore, some of the present compounds exhibit no significant phytotoxicity on the crops.
The present compounds also have herbicidal activity against various weeds which may cause some trouble in the flooding treatment on paddy fields, such as listed below.
Graminaceous Weeds
barnyardgrass (Echinochloa oryzicola)
Scrophulariaceous Weeds
common falsepimpernel (Lindernia procumbens)
Lythraceous Weed
Indian toothcup (Rotala indica), red stem (Ammannia multiflora)
Elatinaceous Weeds
waterwort (Elatine triandra)
Cyperaceous Weeds
smallflower umbrella sedge (Cyperus difformis), hardstem bulrush (Scirpus juncoides), needle spikerush (Eleocharis acicularis), water nutgrass (Cyperus serotinus), water chestnut (Eleocharis kuroguwai)
Pontederiaceous Weeds
monochoria (Monochoria vaginalis)
Alismataceous Weeds
arrowhead (Sagittaria pygmaea), arrowhead (Sagittaria trifolia), waterplantain (Alisma canaliculatum)
Potamogetonaceous Weeds
roundleaf pondweed (Potamogeton distinctus)
Umbelliferous Weeds
watercelery sp. (Oenanthe javanica)
Furthermore, some of the present compounds exhibit no significant phytotoxicity on transplanted paddy rice.
The present compounds can also attain the control of a wide variety of weeds which are growing or will grow in the other non-cultivated lands in which weed controlling is necessiated such as levee, riverbed, roadside, railroad, green field of park, ground, parking, airport, industrial place (ex. factory, storage equipement), fallow land, vacant lot, and the like, orchards, grasslands, lawns, forests. The present compounds also have herbicidal activity against various aquatic weeds, such as water hyacinth (Eichhornia crassipes), which are growing or will grow at the waterside such as rivers, canals, waterways or reservoir.
The present compounds have substantially the same characteristics as those of the herbicidal compounds disclosed in the published specification of International Patent Application, WO95/34659. In the case where crops with tolerance imparted by introducing a herbicide tolerance gene described in the published specification are cultivated, the present compounds can be used at larger rates than those used when ordinary crops without tolerance are cultivated, which makes it possible to control other unfavorable weeds more effectively.
When the present compounds are used as the active ingredients of herbicides, they are usually mixed with solid or liquid carriers or diluents, surfactants, and other auxiliary agents to give emulsifiable concentrates, wettable powders, flowables, granules, concentrated emulsions, water-dispersible granules, or other formulations.
These formulations may contain any of the present compounds as an active ingredient at an amount of 0.001 to 80% by weight, preferably 0.005 to 70% by weight, based on the total weight of the formulation.
The solid carrier may include, fine powders of mineral matters such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, and calcite; fine powders of organic substances such as walnut shell powder; fine powders of water-soluble organic substances such as urea; fine powders of inorganic salts such as ammonium sulfate; and fine powders of synthetic hydrated silicon oxide. The liquid carrier may include, aromatic hydrocarbons such as methylnaphthalene, phenylxylylethane, and alkylbenzene (e.g., xylene); alcohols such as isopropanol, ethylene glycol, and 2-ethoxyethanol; esters such as phthalic acid dialkyl esters; ketones such as acetone, cyclohexanone, and isophorone; mineral oils such as machine oil; vegetable oils such as soybean oil and cottonseed oil; dimethyl sulfoxide, N,N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water and the like.
The surfactant used for emulsification, dispersing, or spreading may include surfactants of the anionic type, such as alkylsulfates, alkylsulfonates, alkylarylsulfonates, dialkylsulfosuccinates, and phosphates of polyoxyethylene alkyl aryl ethers; and surfactants of the nonionic type, such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.
The other auxiliary agent may include lignin sulfonates, alginates, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), and PAP (isopropyl acid phosphate).
The present compounds are usually formulated and then used for soil, foliar, or flooding treatment at pre- or post-emergence of weeds. The soil treatment may include soil surface treatment and soil incorporation. The foliar treatment may include application over the plants and directed application in which a chemical is applied only to weeds so as to keep off the crop plants.
The present compounds may often exhibit the enhancement of herbicidal activity when used in admixture with other herbicides. They can also be used in admixture with insecticides, acaricides, nematocides, fungicides, bactericides, plant growth regulators, fertilizers, and soil conditioners.
Such herbicides are shown below, atrazine, cyanazine, dimethametryn, metribuzin, prometryn, simazine, simetryn, chlorotoluron, diuron, fluometuron, isoproturon, linuron, methabenzthiazuron, propanil, bentazone, bromoxynil, ioxynil, pyridate, butamifos, dithiopyr, ethalfluralin, pendimethalin, thiazopyr, trifluralin, acetochlor, alachlor, butachlor, diethatyl-ethyl, dimethenamid, fluthiamide, mefenacet, metolachlor, pretilachlor, propachlor, cinmethylin, acifluorfen, acifluorfen-sodium, benzfendizone, bifenox, butafenacil, chlomethoxynil, fomesafen, lactofen, oxadiazon, oxadiargyl, oxyfluorfen, carfentrazone-ethyl, fluazolate, flumiclorac-pentyl, flumioxazine, fluthiacet-methyl, isopropazol, sulfentrazone, thidiazimin, azafenidin, pyraflufen-ethyl, cinidon-ethyl, difenzoquat, diquat, paraquat, 2,4-D, 2,4-DB, clopyralid, dicamba, fluroxypyr, MCPA, MCPB, mecoprop, quinclorac, triclopyr, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethoxysulfuron, flazasulfuron, flucarbazone, flumetsulam, flupyrsulfuron, halosulfuron-methyl, imazosulfuron, indosulfuron, metosulam, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, procarbazone-sodium, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, triasulfuron, tribenuron-methyl, tritosulfuron, thifensulfuron-methyl, triflusulfuron-methyl, pyribenzoxim, bispyribac-sodium, pyriminobac-methyl, pyrithiobac-sodium, imazameth, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, tepraloxydim, alloxydim-sodium, clethodim, clodinafop-propargyl, cyhalofop-butyl, dichlofop-methyl, fenoxaprop-ethyl, fenoxaprop-p-ethyl, fluazifop-buthyl, fluazifop-p-butyl, haloxyfop-methyl, quizalofop-p-ethyl, sethoxydim, tralkoxydim, diflufenican, flurtamone, norflurazone, benzofenap, isoxaflutole, pyrazolate, pyrazoxyfen, sulcotrione, clomazone, mesotrione, isoxachlortole, bialaphos, glufosinate-ammonium, glyphosate, sulfosate, dichlobenil, isoxaben, benthiocarb, butylate, dimepiperate, EPTC, esprocarb, molinate, pyributicarb, triallate, diflufenzopyr, bromobutide, DSMA, MSMA, cafenstrol, daimron, epoprodan, flupoxam, metobenzuron, pentoxazone, piperophos, triaziflam, beflubutamid, benzobicyclon, clomeprop, fentrazamide, flufenacet, florasulam, indanofan, isoxadifen, mesotrione, naploanilide, oxaziclomefone, pethoxyamid, phnothiol, pyridafol
The above compounds are described in the catalog of Farm Chemicals Handbook, 1995 (Meister Publishing Company); AG CHEM NEW COMPOUND REVIEW, VOL. 13, 1995, VOL. 15, 1997, VOL. 16, 1998 or, VOL. 17, 1999 (AG CHEM INFORMATION SERVICES) or Josouzai Kenkyu Souran (Hakuyu-sha).
When the present compounds are used as the active ingredients of herbicides, the application amount, although it may vary with the weather conditions, formulation types, application times, application methods, soil conditions, crops to be protected, and weeds to be controlled, is usually in the range of 0.01 to 20,000 g, preferably 1 to 12,000 g, per hectare. In the case of emulsifiable concentrates, wettable powders, flowables, concentrated emulsions, water-dispersible granules, or the like, they are usually applied after diluted in their prescribed amounts with water (if necessary, containing an adjuvant such as a spreading agent) at a ratio of 10 to 1000 liters per hectare. In the case of granules or some types of flowables, they are usually applied as such without any dilution.
The adjuvant which can be used, if necessary, may include, in addition to the surfactants as described above, polyoxyethylene resin acids (esters), lignin sulfonates, abietates, dinaphthylmethanedisulfonates, crop oil concentrates, and vegetable oils such as soybean oil, corn oil, cottonseed oil, and sunflower oil.
The present compounds can also be used as the active ingredients of harvesting aids such as defoliants and desiccants for cotton (Gossipyum spp.), and desiccants for potato (Solanum tuberosum). In these cases, the present compounds are usually formulated in the same manner as the case where they are used as the active ingredients of herbicides, and used alone or in admixture with other harvesting aids for foliar treatment before the harvesting of crops.